Kinetics, mechanism, and stereochemistry of Diels‐Alder reactions of CN‐substituted ethenes with cyclohexa‐1, 3‐diene in the gas phase | Zendy

Van Mele B. | Zendy; Huybrechts G. | Zendy

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Kinetics, mechanism, and stereochemistry of Diels‐Alder reactions of CN‐substituted ethenes with cyclohexa‐1, 3‐diene in the gas phase

Author(s) -

Van Mele B.,

Huybrechts G.

Publication year - 1987

Publication title -

international journal of chemical kinetics

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.341

H-Index - 68

eISSN - 1097-4601

pISSN - 0538-8066

DOI - 10.1002/kin.550190407

Subject(s) - chemistry , diene , kinetics , gas phase , reaction mechanism , stereochemistry , medicinal chemistry , organic chemistry , catalysis , physics , natural rubber , quantum mechanics

The kinetics of the Diels‐Alder additions of CH 2 = CHCN, CH 2 = C(CH 3 ) CN, and cis ‐ and trans ‐CH 3 CH = CHCN to cyclohexa‐1, 3‐diene have been studied in the gas phase. The stereochemistry of these reactions is discussed. In terms of a biradical mechanism, a minimum value of 4.1 ± 0.8 kcal mol −1 for the stabilizing effect of a CN group vis‐à‐vis a methyl group is shown to fit the experimental activation energies.

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